Diisopropylethylamine → HCID 45274820, compound

HRID 1667210Notes

Reaction equation

HRID 1667210 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][C:7]1([CH3:13])[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.[O:19]=[C:20]1[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:22][N:21]1[CH2:37][C:38](O)=[O:39].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][C:7]1([CH3:13])[NH:8][CH2:9][CH2:10][N:11]([C:38](=[O:39])[CH2:37][N:21]2[CH2:22][CH2:23][C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:20]2=[O:19])[CH2:12]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 203639692-(3,4-Dimethoxybenzyl)-2-methylpiperazineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45274820HCID 45274820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(3,4-dimethoxybenzyl)-2-methylpiperazine (0.052 g, 0.208 mmol; German Patent No. DE2438725), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (0.061 g, 0.208 mmol; Example 1C) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.079 g, 0.208 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.054 mL, 0.312 mmol) and the reaction stirred overnight. The reaction was loaded onto silica gel and the product eluted using a gradient of 0.5% methanol/dichloromethane to 5% methanol/dichloromethane containing 7 N NH3 over 30 minutes to provide the title compound. MS (ESI+) m/z 528.2 (M+H)+.

Workup

  1. washthe product eluted
  2. customover 30 minutes

Sources & evidence

ORD record
ord-b4dac419b4774c66952de043d43c31de
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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